氢化-迈森海默络合物的形成和质子化作为红平红球菌对2,4,6-三硝基苯酚生物降解的关键反应。
Hydride-Meisenheimer complex formation and protonation as key reactions of 2,4,6-trinitrophenol biodegradation by Rhodococcus erythropolis.
作者信息
Rieger P G, Sinnwell V, Preuss A, Francke W, Knackmuss H J
机构信息
Institut für Mikrobiologie der Universität Stuttgart, D-70569 Stuttgart, Germany.
出版信息
J Bacteriol. 1999 Feb;181(4):1189-95. doi: 10.1128/JB.181.4.1189-1195.1999.
Abstract
Biodegradation of 2,4,6-trinitrophenol (picric acid) by Rhodococcus erythropolis HLPM-1 proceeds via initial hydrogenation of the aromatic ring system. Here we present evidence for the formation of a hydride-Meisenheimer complex (anionic sigma-complex) of picric acid and its protonated form under physiological conditions. These complexes are key intermediates of denitration and productive microbial degradation of picric acid. For comparative spectroscopic identification of the hydride complex, it was necessary to synthesize this complex for the first time. Spectroscopic data revealed the initial addition of a hydride ion at position 3 of picric acid. This hydride complex readily picks up a proton at position 2, thus forming a reactive species for the elimination of nitrite. Cell extracts of R. erythropolis HLPM-1 transform the chemically synthesized hydride complex into 2,4-dinitrophenol. Picric acid is used as the sole carbon, nitrogen, and energy source by R. erythropolis HLPM-1.
摘要
红平红球菌HLPM-1对2,4,6-三硝基苯酚（苦味酸）的生物降解通过芳环系统的初始氢化作用进行。在此，我们提供了在生理条件下苦味酸及其质子化形式形成氢化物-迈森海默络合物（阴离子σ-络合物）的证据。这些络合物是苦味酸脱硝和微生物有效降解的关键中间体。为了对氢化物络合物进行比较光谱鉴定，首次合成了该络合物。光谱数据显示氢化物离子最初加成在苦味酸的3位。这种氢化物络合物很容易在2位获取一个质子，从而形成用于消除亚硝酸盐的反应性物种。红平红球菌HLPM-1的细胞提取物将化学合成的氢化物络合物转化为2,4-二硝基苯酚。红平红球菌HLPM-1将苦味酸用作唯一的碳源、氮源和能源。
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